IP Library Granted Patent US 7,368,613
Granted Patent B2
US 7,368,613 · App. 11/422,917 · Granted May 6, 2008

Sandal fragrances

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Quick Facts
Patent No.
US 7,368,613
App. No.
11/422,917
Granted
May 6, 2008
Kind
B2
Abstract

A compound of formula (Ia) or (Ib), wherein in each of formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 , and the use thereof as a sandalwood fragrance.

Claims (30)

1. Compound of formula (Ia) or (Ib)

wherein in each of the formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 .

2. Compound according to claim 1 , wherein the compound is present in the form of

(a) a pure optically active enantiomer,

(b) a racemic mixture of different enantiomers of the diastereoisomeric enantiomer pairs, or

(c) an optically active mixture of different enantiomers.

3. Compound according to claim 1 , wherein:

R 1 is CH 3 , and

R 2 is H.

4. Mixture comprising a compound of formula (Ia) and a compound of formula (Ib)

wherein in each of the formulae (Ia) and (Ib) R 1 and R 2 , independently of one another, are H or CH 3 .

5. Mixture according to claim 4 , R 1 and R 2 in the compound of formula (Ia) are the same as in the compound of formula (Ib).

6. Mixture according to claim 5 , comprising or wherein both in the compound of formula (Ia) and in the compound of formula (Ib)

R 1 is CH 3 , and

R 2 is H.

7. Fragrance composition having a sandalwood odour, comprising a compound according to claim 1 .

8. Fragrance composition according to claim 7 further comprising a carrier or substrate which is in direct contact with said compound.

9. Process for the preparation of a compound according to claim 1 , comprising:

reducing a compound of formula (IXa) or (IXb)

wherein R 1 represents H or CH 3 , to form a compound according to claim 1 wherein R 2 is H.

10. Process according to claim 9 further comprising methylating said compound by nucleophilic addition of an organometallic compound of methyl anion nature to said compound to form a compound wherein R 2 is CH 3 .

11. Process for the preparation of a compound of formula (Ia)

wherein

R 1 represents H or CH 3 , and

R 2 represents H, comprising the following steps:

forming an aldehyde of formula (IXa) wherein R 2 ═H by an epoxide ring-opening reaction of a compound of formula (XIV) and

reducing said aldehyde of formula (IXa) to form a compound of formula (Ia) wherein R 1 , R 2 ═H, or

methylating said aldehyde of formula (IXa) by nucleophilic addition of an organometallic compound of methyl anion nature to the aldehyde, to form said compound of formula (Ia) wherein R 1 ═CH 3 , and R 2 ═H.

12. Method of producing, enhancing or modifying a sandalwood odour in a formulation, comprising the following steps:

mixing one or more compounds according to claim 1 with said formulation in an amount that is sufficient (a) to produce a sandalwood odour in the resulting mixture, (b) to enhance an existing sandalwood odour in said formulation.

Assignments (2)
MERGER Recorded Apr 22, 2011
From: SYMRISE GMBH & CO. KG
To: SYMRISE AG
Reel/Frame 026171/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2006
From: EH, MARCUS
To: SYMRISE GMBH & CO. KG
Reel/Frame 017744/0633 →